---
title: 'Deployment Strategist at Tailwind'
canonical: 'https://feeny.ai/job/deployment-strategist-tailwind-san-francisco-whd36eqjgk8f'
type: 'job'
last_seen: '2026-09-08'
---

# Deployment Strategist at Tailwind

- **Company:** Tailwind
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2025-08-29
- **Last confirmed live:** 2026-09-08
- **Apply:** https://jobs.ashbyhq.com/tailwind/3693a299-ddff-43f4-8edd-ad8315739db4

## Job description

## ABOUT TAILWIND

Tailwind is organizing the world's insurance information.

Insurance is one of the largest markets in the world, and it runs entirely on PDFs and antiquated infrastructure. We like it that way. While the industry takes years to roll out change, we ship in days.

Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.

## ABOUT THE ROLE

We’re a tight-knit team moving fast — the kind of place where you’ll work directly with leadership, wear many hats, and see your ideas in production fast.

As a Deployments Strategist you’ll work at our office in San Francisco and own the journey from “signed customer” to “activated teams of users.” You’ll design and execute onboarding plans, run kickoff and training sessions, and own the technical integration (mostly SQL). You may need to travel to customers from time-to-time (< 20%).

A great candidate will be someone who loves creating order out of ambiguity and making customers feel like they’re in great hands.

## WHAT YOU’LL DO

- Lead onboarding projects for new customers, ensuring timely and successful product adoption
- Run engaging kickoff calls, training sessions, and Q&A meetings
- Own technical integration for your customers (SQL, Cloud Platforms)
- Identify opportunities to partner with customers to deliver new product or project based consulting engagements
- Build and maintain onboarding materials: playbooks, quick start guides, how-to videos, and FAQs
- Track progress against onboarding milestones and proactively address roadblocks

## WHAT MAKES YOU A GREAT FIT

- 3–5 years of work experience in consulting, or in customer facing roles at a SaaS company
- Experience juggling multiple deployments/projects at once
- Exceptional written and verbal communication skills — you can make complex concepts easy to understand
- Comfort operating in a fast-changing, resource-constrained startup environment
- Empathy for customers combined with a bias toward action

## WHY YOU SHOULD WORK HERE

- Direct impact on customer satisfaction and retention
- There are 2 ingredients to achieving high growth in your career; be great at your job, be a part of a fast growing company. We have one of those, the other is up to you.
- Opportunity to see how the latest AI is being applied to solve high value problems
- Our core team has worked together 3 times now, hailing from Carta ($7B) and AppDirect ($2B) and includes veterans from Ramp, Apple, Salesforce and C3 AI
- Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions
- We’re in-person at our beautiful offices 5 days per week in San Francisco (financial district). If you want to do the most meaningful work of your career, with an elite team, in a trillion dollar market, come join us!

## About Tailwind

## Company Overview
- **One-liner**: AI-powered loss run automation platform that provides end-to-end stewardship analytics for commercial insurance brokerages.
- **Entity Type**: Private (Startup – Seed stage)
- **Headquarters**: San Francisco, California, USA (with a secondary presence in Canada)
- **Founded**: 2020
- **Founders**: Michael Heider (CEO & Co-Founder)

## Core Business
- **Industry**: Insurance Technology (Insurtech) – specifically workflow automation for commercial Property & Casualty (P&C) insurance.
- **Target Customers**: B2B – Insurance agencies, brokerages, MGAs, and wholesalers across the U.S.
- **Mission/Purpose**: “Power stewardship reports for your entire book and new business” – enabling brokers to become trusted advisors by eliminating manual data retrieval and analysis.

## Products & Services
- **Loss Run Automation**: Automated scheduling and retrieval of loss runs from carriers, wholesalers, and MGAs. Includes real-time experience modification (Ex Mod) snapshots and projections.
- **Stewardship Reports**: Client-facing analytics reports for every policy across every carrier, featuring trend analysis, loss summaries, and benchmarking.
- **Proposals**: Customizable, brand-tailored client proposals with side-by-side quote comparisons.
- **Policy Checking**: Automated verification of policy details against quotes and submissions to ensure accuracy and coverage.
- **Quote Comparison**: Multi-market quote comparison to quickly identify the best coverage options.
- **Benchmarks**: Compare loss ratios, mods, and rates across carriers and regions.

All products are delivered as a SaaS platform.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (private company).
- **Key Metric**: Total Funding – $50,000 USD (Pre-Seed round, March 2024). Annual revenue is not publicly available.
- **Notable Investors/Partners**: Lead investor – BrokerTech Ventures (Pre-Seed). Also Microsoft Partner Verified.
- **Notable Customers**: Moody Insurance Agency, M3 Insurance, Unico, Newfront, Marshall Sterling, Baldwin, CGO, Propel, True North, HIG.
- **Growth Signals**: Headcount grew +1,100% year-over-year (to 19 employees as of mid-2026). Active hiring with 8 open roles across engineering, sales, and customer success.

## Competitive Advantages
- **SOC 2 Type II Certified** and **Microsoft Partner Verified** with bank-level data encryption.
- Automated connectivity to **1,000+ carriers, wholesalers, and MGAs**.
- AI-driven end-to-end automation saves brokers **10+ hours per renewal**.
- Comprehensive platform covering loss run retrieval, analytics, proposals, policy checking, and benchmarking – all in one place.

## Strategic Focus
- Scale automated stewardship reporting to the entire book of business (both renewal and new business).
- Deepen integrations with agency management systems and CRM platforms.
- Expand client base among top U.S. brokerages and increase market share in the commercial P&C space.

## Why Work Here
- **Culture**: Fast-growing startup (headcount up 1,100% YoY) with a focus on execution and innovation.
- **Work Policy**: Hybrid model (in-office for San Francisco-based roles; some roles in-office). San Francisco HQ is pet-friendly with free snacks and drinks.
- **Perks & Benefits**: Company equity, performance bonuses, generous parental leave, family medical leave, dental & health insurance, Flexible Spending Account (FSA), commuter benefits, job training & conferences, and customized development tracks.
- **Engineering Culture**: Emphasis on product and forward-deployed engineering; currently hiring Frontend Product Engineers, Full Stack Engineers, and Forward Deployed Engineers.

## Sources
1. [ontailwind.com](https://www.ontailwind.com/)
2. [builtin.com](https://builtin.com/company/tailwind-ontailwind)
3. [linkedin.com](https://www.linkedin.com/company/ontailwind)
4. [insurtechlist.com](https://insurtechlist.com/companies/tailwind/)
5. [scoutify.com](https://scoutify.com/companies/tailwind/)

## Other roles at Tailwind

- [Forward Deployed Engineer](https://feeny.ai/job/forward-deployed-engineer-tailwind-san-francisco-5nmpfvh54rns) — San Francisco, CA
- [Frontend Product Engineer](https://feeny.ai/job/frontend-product-engineer-tailwind-toronto-pnn06mxpb29h) — Toronto, Canada
- [Account Executive](https://feeny.ai/job/account-executive-tailwind-san-francisco-basbbcqmtxh0) — San Francisco, CA
- [Sales Development Representative](https://feeny.ai/job/sales-development-representative-tailwind-san-francisco-atzm72063zkj) — San Francisco, CA
- [Product Operations](https://feeny.ai/job/product-operations-tailwind-san-francisco-fb0v72r2k078) — San Francisco, CA
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